Process for the preparation of aryloxyphenoxypropionic acid derivatives in a non polar solvent with a tertiary amine catalyst

Abstract

A process for the preparation of an aryloxyphenoxypropionic acid derivative compound of formula I (formula I) wherein Ar is an aryl group, R′ is selected from the group consisting of hydrogen, linear or branched aliphatic, alkoxyalkyl, alicyclic, aralkyl, haloaryl, alkylideneamino-oxyalkyl or heterocyclyl alkyl group, X is selected from NR′ or O, and R′ is selected from the group consisting of hydrogen, linear or branched aliphatic group, which comprises the reaction in a nonpolar solvent of a phenolpropionic acid derivative compound of formula II (formula II) with a haloarene compound of formula Ar—Y when Y is a halogen atom, in the presence of an inorganic or organic base and a catalyst selected from the group of tertiary amines.

1 . A process for the preparation of an aryloxyphenoxypropionic acid derivative compound of formula I 
       
         
           
           
               
               
           
         
         wherein Ar is an aryl group, R′ is selected from the group consisting of hydrogen, linear or branched aliphatic, alkoxyalkyl, alicyclic, aralkyl, haloaryl, alkylideneamino-oxyalkyl or heterocyclyl alkyl group, X is selected from NR″ or O, and R″ is selected from the group consisting of hydrogen, linear or branched aliphatic group, which comprises the reaction in a nonpolar solvent of a phenolpropionic acid derivative compound of formula II 
       
       
         
           
           
               
               
           
         
         with a haloarene compound of formula Ar—Y when Y is a halogen atom, in the presence of an inorganic or organic base and a catalyst selected from the group of tertiary amines. 
       
     
     
         2 . The process according to  claim 1 , wherein the water formed as byproduct is removed from the reaction. 
     
     
         3 . The process according to  any of previous claims , wherein the temperature of the reaction is in the range from 60 to 200° C. 
     
     
         4 . The process according to  any of previous claims , wherein the pressure of the reaction is normal atmospheric pressure or reduced pressure. 
     
     
         5 . The process according to  any of previous claims , wherein the nonpolar solvent is a hydrocarbon solvent which optionally contains halogen atoms. 
     
     
         6 . The process according to  any of previous claims , wherein the inorganic base is selected from the group consisting of an alkali metal, alkaline earth metal or ammonium carbonate, bicarbonate, phosphate, hydrogen- or dihydrogenphosphates. 
     
     
         7 . The process according to  any of previous claims , wherein the amount of the inorganic or organic base ranges from 1 to 5 moles by mole of the haloarene compound of formula Ar—Y. 
     
     
         8 . The process according to  any of previous claims , wherein the catalyst is a bridged bicyclic tertiary amine. 
     
     
         9 . The process according to  claim 8 , wherein the bridged bicyclic tertiary amine is an aliphatic bridged bicyclic tertiary amine. 
     
     
         10 . The process according to  claim 9 , wherein the aliphatic bridged bicyclic tertiary amine is selected from the group consisting of 1,4-diazabicyclo[2.2.2]octane, quinuclidine or tropane. 
     
     
         11 . The process according to  any of previous claims , wherein the amount of catalyst ranges from 0.01% to 50% by mole of the moles of the haloarene compound of formula Ar—Y. 
     
     
         12 . The process according to  any of previous claims , wherein the aryl group Ar is selected from the group consisting of substituted phenyl, substituted 2-pyridinyl, substituted 2-benzoxazolyl, substituted 2-quinoxalinyl, substituted 2-benzothiazolyl, substituted naphthyl or substituted 2-benzimidazole, wherein the substituents are selected from the group consisting of halogen, aliphatic, halo aliphatic, alkoxy, thioalkyl, cyano or nitro groups. 
     
     
         13 . The process according to  any of previous claims , wherein the R′ group is selected from the group consisting of hydrogen, linear or branched alkyl, alkynyl, alkoxyalkyl, aralkyl, haloaryl, alkylideneamino-oxyalkyl or heterocyclyl alkyl group. 
     
     
         14 . The process according to  any of previous claims , wherein X is selected from NR″ or O, and R″ is selected from the group consisting of hydrogen, linear or branched alkyl group. 
     
     
         15 . The process according to  any of previous claims , wherein molar ratio of the phenolpropionic acid derivative compound of formula II versus the haloarene compound of formula Ar—Y ranges from 0.9:1 to 2.5:1.